3-Bromophenol → 1-(diphenylmethyl)-3-hydroxy-3-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3-dihydro-2H-indol-2-one

HRID 2385116Notes

Reaction equation

HRID 2385116 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].BrC1C=C(O)C=CC=1.[C:20]1([CH:26]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29](=[O:36])[C:28]2=[O:37])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.FC(F)(F)C1OC(CN2C3C(=CC=CC=3)C(=O)C2=O)=CC=1>>[C:38]1([CH:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]([OH:36])([C:3]3[C:2]([OH:11])=[CH:1][C:10]4[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=4[CH:4]=3)[C:28]2=[O:37])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

5

Reactant 4

HCID 115633-BromophenolHCID 143055,6,7,8-Tetrahydro-2-naphtholHCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 673564881-((5-(Trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dione

Product 1

HCID 685973231-(diphenylmethyl)-3-hydroxy-3-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2A and making non-critical variations using 5,6,7,8-tetrahydro-2-naphthol to replace 3-bromophenol, and 1-(diphenylmethyl)-1H-indole-2,3-dione to replace 1-((5-(trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dione, 1-(diphenylmethyl)-3-hydroxy-3-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3-dihydro-2H-indol-2-one was obtained (76%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 8.73 (s, 1H), 7.52-7.49 (m, 1H), 7.32-7.28 (m, 10H), 7.09 (dd, J=5.6, 3.2 Hz, 2H), 6.95 (s, 1H), 6.75 (s, 1H), 6.51-6.48 (m, 2H), 4.31 (s, 1H), 2.70 (br s, 2H), 2.52 (br s, 2H), 1.72 (br s, 4H); MS (ES+) m/z 444.1 (M−17).

Sources & evidence

ORD record
ord-c0323e6d01c345f2908a5bd408589cd2
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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